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Total synthesis of isokidamycin.

ABSTRACT: The synthesis of isokidamycin, which represents the first total synthesis of a bis-C-aryl glycoside natural product in the pluramycin family, has been completed. The synthesis features the use of a silicon tether as a disposable regiocontrol element in an intramolecular Diels-Alder reaction between a substituted naphthyne and a glycosyl furan and a subsequent O?C-glycoside rearrangement.

SUBMITTER: O'Keefe BM

PROVIDER: S-EPMC2974561 | biostudies-literature | 2010 Nov

REPOSITORIES: biostudies-literature

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Total synthesis of isokidamycin.

O'Keefe B Michael BM Mans Douglas M DM Kaelin David E DE Martin Stephen F SF

Journal of the American Chemical Society 20101101 44

The synthesis of isokidamycin, which represents the first total synthesis of a bis-C-aryl glycoside natural product in the pluramycin family, has been completed. The synthesis features the use of a silicon tether as a disposable regiocontrol element in an intramolecular Diels-Alder reaction between a substituted naphthyne and a glycosyl furan and a subsequent O→C-glycoside rearrangement. ...[more]

PMID: 20958036

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